Caught Crossdressing by Aunt Sharon
by Kresha Matay
Part I
"I wonder where Brad is? He knows you're coming, you'd think he'd
stick around. Oh, I hope he'll turn up soon, otherwise you'll have to
drive back in the dark."
"Rita, don't worry about the boy so much. Brad is like every other
sixteen year old boy. He's probably driving around with his friends
looking for girls and forgot I was coming!"
"Well, aah, I don't think so!" His mother stumbled to say. "That's
something you and I should probably talk about before you leave. Your
nephew is somewhat different from what you might expect from the
average sixteen year old boy. Sharon, you haven't seen him in over a
year, he's changed. He doesn't spend much time with the other boys in
the area, he seems to be more a loner."
Rita and Sharon were sisters. Rita, Brad's mother was thirty-five,
married to Tom and lived the unsatisfied existence of the average house
wife. She had been a lovely girl in her youth, attracting quite a bit
of attention from all the boys. In her senior year, she fell in love
with Tom Hennesey, the high-school football team's star quarter back.
After the victory dance, convinced that Tom also loved her, she agreed
to go to a local motel with him. Tom, typical of most boys that age,
had been neither gentle, nor concerned with her needs, only interested
in his own satisfaction. She'd lost her "maidenhead", suffered
considerable pain, was not sexually satisfied, and needless to say was
confused by Tom's selfishness. Even worse, she became pregnant with
Brad. Tom and Rita discussed their alternatives, agreed to marry and
with the help of both sets of parents, set up housekeeping. Over the
years, all her dreams of the good life went out the window. With
nothing to look forward to, Rita eventually slipped into a casual
attitude towards her appearance. She gained thirty pounds, wore less
attractive clothes and became exactly what she looked like ... an
average mother/housewife.
Rita was secretly jealous of her sister Sharon. Not because Sharon was
younger by seven years, but because her life was more interesting and
exciting. Sharon was the real beauty of the two sisters. She had
enjoyed the attention her looks brought her, but was wise enough not to
get trapped as Rita had done. Boys, and later men, never became so
important in her life that she sacrificed any of her goals for them.
Sharon was 5'9" tall, perfectly proportioned (possibly a bit too large
in the chest), with long dark hair. Her features where chiseled in the
classic mold of a young Liz Taylor. Every man or woman she met was
immediately struck by desire or jealousy ... sometimes both.
Sharon had started working at a bank right after graduating college in
a management training program. This meant she started out as a
low-paid teller and if she did well she would move up the ladder. It
was the typical way banks were able to get college educated women to
work for them at low salary levels. Her work performance and beauty
got her noticed by the President of the bank, who made her his
administrative assistant. After the first month, in the new position,
her boss came to her and asked her out to dinner, supposedly to discuss
her performance. For the next twelve weeks he courted her lavishly,
showering her with gifts, then asking for her hand in marriage. Sharon
thought long and hard before reaching a decision. He was a nice enough
man and offered her the opportunity of a wealthy lifestyle. Even
though he was thirty-five years her senior, she felt that was of little
consequence. Sharon was worldly enough to understand why he wanted to
marry her. She didn't love him and they both knew it. Therefore, when
he promised to be less than demanding ... sexually, she was tempted to
say yes, but she still hesitated. What finally convinced her to marry
him was his offer of a pre-nuptial agreement. The agreement guaranteed
her a large settlement, after seven years of marriage ... or his
death, whichever came first.
For three years her life was a whirlwind of parties, expensive clothes,
cars and travel. As far as intimacy, he kept his promise. Sex to her
husband was the typical "slam, bam, thank you ma'am, once a month
event". This was more to reassure his aging male ego, than for any
other reason. She "suffered" through those nights bolstered by the
knowledge that the marriage would end in seven years and she would be
set for life. When she was notified of the commuter plane crash and
his confirmed death, she shed not a tear. The fact that she inherited
everything "helped" console her and when an out-of-state bank offered
her a huge price for her controlling bank shares, she found she was now
a twenty-five year old widow with more money than she had ever dreamed
possible.
Sharon had offered a large piece of the inheritance to her sister, but
Rita's husband had refused to accept any of the "blood money". This
refusal caused an uncomfortable split between Sharon and her
brother-in-law. She only visited when she was sure Tom was away on
business. Rita in order to keep peace couldn't even call her sister
since Tom checked the long-distance phone bills. This didn't stop
Sharon from calling and keeping in touch with Rita and Brad. Whenever
she did visit, she would insist on taking both of them shopping and
then out to dinner at the most expensive restaurants and stores. This
was her way of making up for not being there on a regular basis. Brad,
of course, loved when his Aunt came to visit, what young boy wouldn't.
As he grew older he began to realize that she never visited when his
father was around. This hurt him deeply. His Aunt was the person he
loved the most.
Tom, Rita and Brad didn't have a peaceful homelife. Father and son
felt no warmth towards each other. Brad had not inherited his father's
physical prowess and was a definite disappointment to Tom. This
worsened the home situation even more, to the point that Brad began to
"hate" his father and Tom, in response, further ignored his son. Rita
was confused by her love for her son versus her love for Tom. This
sent mixed signals to Brad. Because he received no emotional
satisfaction at home, Brad replaced a child's normal affection for his
parents with affection for his Aunt and wished he lived with her. He
turned this desire to live with her into a fantasy in which he was her
son instead of Rita's.
As many young boys do, he began to use her image in his sexual
fantasies. After his first fantasy, in which she seduced him, he was
hit with guilt induced tears and promised himself he would never again
view his Aunt as a sex object. However, the next time he got the urge
to masturbate, Aunt Sharon again appeared as the sensual woman in his
fantasy. With each fantasy re-enactment his guilt lessened.
Tom felt that Brad was the reason he had been "trapped" into marrying
Rita. Oh, he assumed he loved his wife, but still wished they had
waited to marry till he had sown a few "wild oats". Besides, Rita no
longer looked like the woman he had married and no longer excited him.
More and more, he found himself thinking of having an affair with a
secretary where he worked. These frustrations manifest themselves in
the form of mental and physical abuse towards Brad, who sought refuge
in his confused mother's arms. This strained situation continued till
one day Brad, in a fit of anger, shouted at his father.
"I wish I could go and live with Aunt Sharon so I could get away from
you!"
His father was just as quick to answer, "If she'll take you, you can
leave right now!"
Rita, realizing where this was heading, stepped between father and son
and quickly suggested Brad "visit" his Aunt for the entire summer.
Then when summer was over, everyone would sit down and talk the
situation through and come to a resolution. She hoped that this
cooling off period would bring about a reconciliation. That's why
Sharon had come, to take Brad back to Columbus to live with her.
Rita was also concerned by changes she noticed in her son's behavior.
At first, she suspected what every parent fears ... drugs. But after
reading about the symptoms and realizing they weren't present in Brad's
behavior patterns, she accepted Brad's behavior as the outward effects
of puberty. Rita had caught her son looking up her skirt, down her
blouse and peeking through the bedroom keyhole. While this made her
uncomfortable and she criticized his actions, she secretly enjoyed
knowing he found his mother attractive enough to spy upon. Brad's
spying made her feel wanted, now that her relationship with her husband
had soured. In addition, Brad showed interest in feminine clothing,
especially women's undergarments (he used his mother's panties to bring
himself to orgasm). She discovered unexplained runs in her pantyhose
and misplaced articles of her lingerie. While she didn't understand
all the actions, some were easily explained by the fact he was "growing
up".
One day, left alone in the house he decided, "If the panties feel so
good against my dick, I wonder how they'd feel if I wear them?" This
was his first step into crossdressing, but only the first. From that
moment, whenever he was alone, he would sneak into his mother's room,
carefully open her lingerie drawers and borrow a bra, panties and hose.
His mother never kept her drawers neat, so she never discovered his
temporary thefts. He continued dressing up in the borrowed feminine
clothing, experimenting and actually becoming relatively adept at
wearing his mother's attire. He also practiced feminine mannerisms in
front of a full-length mirror. When dressed and standing before the
mirror he created fantasy conversations speaking in a girlish voice
which he managed to develop with practice.
Once tempted, his young mind became obsessed with women, their clothes
and their bodies. He became an expert on lingerie and foundation
garments. He discovered the purpose each item fulfilled towards
enhancing a woman's figure. Matching his mother's lingerie labels
against the descriptions in the catalogs he learned to distinguish the
subtle differences of each material. Using this same method, he
studied dresses, skirts and blouses. Diligently applying himself, he
soon became expert enough to determine what a woman was wearing and the
material from which it was made.
Hearing a noise, both women looked up as the front door opened and Brad
walked in. Seeing his beloved Aunt, he rushed to her and leaned over
to give her a hug and kiss. In his excitement to see her, he lost his
balance and fell across her lap, his right hand falling between her
nylon clad thighs. Sharon's instinctive reaction was to close her
legs, thereby trapping his hand against the firm flesh of her upper
thighs. The absurdity of the situation became immediately apparent and
the women began to roar in uncontrollable laughter. This gave Brad the
opportunity to extricate his hand and right himself. Embarrassed, he
offered profuse apologies to both women, but especially his Aunt.
"It's alright Brad," she stated. "I know it was just an accident, it's
better it happened here, instead of in the presence of strangers.
Besides, it's been a long time since I've had that much fun with such
an aggressive young man," she teased.
Brad, was embarrassed. Not knowing what to say, he stood there trying
to hide the blush plastered across his features and the erection in his
pants. Rita, seeing the bulge in her son's pants, realized her son's
predicament. Catching her sister's attention, she silently
communicated the situation, as all grown women are able to do. Sharon,
understood immediately. Rising, she threw her arms around Brad and
whispered.
"I'm only kidding, don't be embarrassed, nothing serious happened and
no damage was done. Afterall, I'm your Aunt. If your going to live
with me this summer we'll probably have other accidents around the
house. Don't let what happened embarrass you. It doesn't bother me,
so don't let it bother you. Now give me a big kiss to make it all
better."
Brad, kissed his Aunt and asked, "Am I really going to live with you
all summer?"
"Of course, it's all decided. In fact, since I have a dental
appointment tomorrow, we're driving back right after lunch. That way
we'll have time to get you all settled in. Are you packed?"
Rita started laughing, "He's been packed for two days, you'd think he
'hated' being with his mother", she chided.
"Oh mom! It's not you, I'll miss you, it's just ... well you know."
"Yes dear, I know. Don't worry I understand. Now let's have that
lunch, so you two can get going."
Part II
After lunch, they loaded the car, said good-bye to Rita and headed out
of Chicago. Aunt Sharon explained that the drive normally took seven
hours, but they would stop for a break in Indianapolis.
Sharon spent the next hour or so asking questions of her nephew. At
first he was evasive, not wishing to disclose anything about the
situation at home, but as he became more comfortable with his Aunt, he
opened up to her. She learned about Tom's abuse and Brad's closeness
with her sister. She discovered that Brad, within the last 18 months,
had also discovered the female gender. Unfortunately for Brad, it had
arrived, just as his relationship with his father had worsened.
After an hour of driving, Sharon turned south on I-65 towards
Indianapolis. This stretch of road is considered one of the most
boring in the mid-west. Flat farm land as far as the eye can see, the
exit signs being the only breaks in the monotony. Traffic was
extremely light so she settled back, in the most relaxed and
comfortable position available and set the cruise control to the speed
limit. Her body adjustments caused her 18" skirt to rise above the
welt of her nylons. She could have easily tugged the hem back in
place, but instead, chose to ignore it. This was the manner in which
she normally drove and decided she wouldn't change her entire lifestyle
because of Brad. Sharon said to herself, "He's only a teenager and
probably thinks of me as a second mother. In fact, I'll suggest that
he view me in that light. If that works, It'll mean fewer changes in
my lifestyle." Glancing over at her nephew to determine the effect of
her exposure, she found him curled up ... asleep. Smiling to herself,
she returned her attention to the road.
Brad wasn't really asleep. He had chosen to avoid further questions by
playing "possum". Peering between his drawn eyelashes he became aware
of his Aunt's exposed thighs. Mumbling softly, as if asleep, he
adjusted his position in order to obtain a better view and at the same
time, moved his hands in order to cover his crotch.
Sharon, hearing him moan, again glanced over at Brad, then smiled down
at him as a thought ran through her mind. "I hope it works out between
us, I think I'd like Brad to live with me on a permanent basis. I've
always wanted my own child. I would've preferred a daughter, and I
wish he were younger, someone I could better relate to, but having a
son like Brad would be wonderful. Of course I'm going to have to make
some adjustments in my lifestyle ... especially Sandy."
She smiled to herself as thoughts of Sandy, her lesbian lover came to
mind. After her husband had died, Sharon found she felt no need to
become romantically involved with another male. Unfortunately, her
sexual needs still existed. She and her roommate, during their college
years, had played "girl games" in the secrecy of their apartment and
had "discovered" each other. Though, she never spoke about those "old"
days, she had enjoyed the sexual experimentation and tender
satisfaction they had shared. Sharon, remembering those blissful
moments decided it was time to try the gentler sex again. After a few
embarrassingly unsuccessful and pathetic attempts, she resigned herself
to masturbation. That's when Sandy came into her life.
Sandy was the bank examiner involved in the audit when Sharon sold her
bank shares. The two women immediately saw something in the other's
eyes, had lunch together, admitted they were strongly attracted to each
other and became lovers. Within a short span of time, Sharon had
invited Sandy to move in with her and Sandy agreed. Sandy's job caused
her to be away for extended periods. When ever she was in town, she
spent every available moment with Sharon. Sharon's realized how much
she missed the "bitchy" blond who shared her bed. Sandy's current
absence, over three weeks, caused sexual desire to creep into her
thoughts. She soon realized, that thinking about Sandy was causing her
pussy to become damp with desire. Slipping her left hand to her inner
thigh, she gently stroked the warm flesh above the welt of her nylons.
Stretching her long nailed index finger under her drawn-up skirt, she
found the tip of her nail was barely short of her panty cover crotch.
Adjusting her hand an inch closer made all the difference in the world.
Now she could "tease" the silky smooth material holding back the puffy
entrance to her woman hood. Drawing her nail slowly upward caused the
tightly drawn nylon panty material to sensually vibrate against her
moist opening. Enjoying the ever increasing exhilaration that came
with each finger-stroke caused her to softly "mew". Still not fully
satisfied with her position, Sharon thrust her hips forward. Now the
nail tip located the demanding bud of her blood-filled clitoris as it
pushed against the now soaked crotch of her panties. Back and forth,
slowly, moving only the last digit on her finger, she flicked the now
protruding mound of flesh, fantasizing it was Sandy tongue instead of
her own finger. Building her passions to the impending brink of
orgasm, she paused, remembering where she was and who sat next to her.
Realization was a bucket of cold water. There was no doubt that her
impending climax would wake Brad. Disappointed, but also adult about
the situation, Sharon chose the respectable course. Giving herself a
last firm flick, she forced her hand away, hiding her actions by an
adjustment of her skirt. With a last look at Brad, to reassure herself
that he was still asleep, Sharon returned her mind and eyes to the
road.
Brad, had seen everything! Disappointed and ecstatic at the same time.
He could now add a touch of sensual realism to his fantasies.
Remembering what he had just witnessed, he really fell asleep, dreaming
of future voyeur episodes he might experience while living with his
Aunt.
The rest of the trip was uneventful. They stopped in Indy, had a snack
and continued their journey. They arrived in Columbus, shortly after
sunset.
Part III
Sharon gave him the grand tour of her home. Brad was truly impressed.
While it wasn't quite a mansion, it was the largest and most luxurious
house he had ever been inside. When she showed him her master bedroom,
he became sexually excited. It was so ultra-feminine, with it's frilly
curtains, lace bedspread and pastel walls and lamps. The room was
dominated by the large "four poster" king-size bed with it's sheer
drapes tied back at the corners. The pictures on the walls were
definitely well suited to the color scheme, if not a bit strange to his
youthful mind. They depicted beautiful naked women, alone or in pairs,
sensually reclining upon couches and beds. The women's genitals
scarcely hidden by a crossed arm, raised thigh or perfectly placed
pillow. Brad was tantalized by the suggestive nature of the paintings
and made a mental note to sneak back into his Aunt's room to further
study the prints. Hiding his erection, he asked.
"Where will I sleep?"
"You can have your choice.", his Aunt answered. "There are two other
bedrooms to choose from. Actually there are three, but the one next to
mine is used by a friend who visits me whenever she's in town. She
keeps some clothes here and rather than move her things, I'm sure
you'll be satisfied with one of the other two. Let me show you."
After being shown both rooms, Brad picked the more feminine of the two.
When his Aunt pointed out he might be more relaxed in the other since
it was "neutral", he stated he particularly liked the feminine bedroom
because it's attached bath room contained a spa type bathtub. He
explained he preferred baths over showers. This explanation more than
satisfied his Aunt, who then recommended a possible redecorating.
Again he assured her it was fine.
"It doesn't bother me, let's not change it until we find out how long
I'll be staying with you."
"Well, if that's all settled do you want me to help you unpack?" She
asked.
"No thanks, Auntie, I can manage. Besides you must be tired from the
long drive, why don't you relax and I'll join you after I'm finished
putting away all my stuff."
Sharon admitted she was tired, wanted to change into more relaxing
clothes and would see him downstairs in the den when he finished
unpacking. Be fore leaving she said.
"Brad, I'm very happy your here and I'm sure we'll get along very well.
However, I want you to understand that it's been a long time since I've
lived with anyone, so I've come to like things a certain way. I'll
expect you to respect and comply with my wishes as if they were your
mother's. In a sense, during your visit, it might even be better if
you think of me that way. You'll have some chores just like at home,
nothing difficult. This is a very large house, but since I like my
privacy, no servants. I have a cleaning lady twice a week who handles
the 'big' stuff, but picking up after yourself, etc., is your
responsibility. We'll talk more about that in the morning. Now if you
don't have any questions, I'm going to clean up a bit and go relax.
Any questions?"
Brad assured her he would do anything to please her, wouldn't be a
bother and thanked her for taking him in for the summer. Throwing his
arms around her, in a surprise move, he hugged and kissed her. The
kiss was just a hint longer than Sharon expected and the hug was also
more familiar. After a few more "thank-you" and "your welcome"
comments ... Sharon left the room.
Brad spent the better portion of an hour unpacking. He had declined
his Aunt's help because he didn't want her to see some of the items in
his suitcases. Along with his normal clothing, he had a cache of
feminine "pretties". These included panties, a bra, a garterbelt and a
pair of nylon hose. He had to find secure hiding places that would not
be discovered by either his Aunt or the cleaning lady. Finally, he
decided to leave them in his supposedly empty suit case which he stored
in the back corner of his walk-in closet. Satisfied, he removed his
clothes, changed into a pair of blue cotton pajamas and went down
stairs to find his Aunt.
Meanwhile, Sharon had also changed into a pair of pajamas. Her's
however, were white satin lounging pajamas with baby pink and blue
designs at the collar and cuffs. Normally, in the evening, she wore
diaphanous peignoir sets around the house, but chose the pajamas since
her nephew was there. Realizing, with regret, that changes were indeed
necessary, she again hoped they could be minimized. Sharon was a woman
who enjoyed being feminine. All her lingerie was the finest, most
expensive available. Oh, it wasn't all that exotic ... just sensual.
One of her pleasures in life was the freedom to express her sensuality
in the privacy of her home. One of the great pleasures of her
existence was the enjoyment of being feminine. The only disappointment
of her sensuality , was she couldn't let anyone other than her lesbian
lover know how much pleasure she derived from secretly expressing her
femininity through her lingerie. As Brad entered the den, Sharon said.
"I thought you might be hungry so I've prepared a snack. It's just
cheese, pat'e and some crackers. If you don't care for pat'e we can
order a pizza or something."
"Pat'e sounds wonderful! I am a little hungry and that will just hit
the spot. I like pat'e. Mom introduced me to it two Christmas's ago
when you sent that gourmet basket."
Brad moved to the couch and sat next to Sharon. They spent the evening
enjoying the snack and each other's company. Every now and then, as
Sharon reached for a morsel of food, Brad caught a glimpse down the
throat of her satin pajamas. He couldn't see much, just the beginning
rise of his Aunt's right breast. He tried to be careful, but thought
she caught him staring at least once. Since she said nothing, he
wasn't sure. Sitting there, next to an adult woman (the woman his
fantasies were built around), in her sexy pajamas, smelling her perfume
and observing the raised "pock" marks her nipples made on the material
was more than he could handle. Thinking about what was barely hidden
behind the material got him excited. Brad developed an erection!
Trying his best to adjust the folds of his pajamas, he dropped a
cracker into his lap.
Sharon had definitely caught him staring down her pajama top.
Realizing he couldn't have seen anything, she excused it as boyish
curiosity and made no effort to adjust her clothing. When she caught
him staring at the nipple marks however, she decided that he needed to
be taught a lesson. When he attempted to adjust his clothing, she
realized he was sporting an erection. Amused, surprised and curious,
she watched as the cracker fell onto his lap. Acting quickly, she
reached her hand into his lap as if to pick up the cracker before it
fell to the carpet. Instead of the cracker her hand encircled his
maleness. It was much bigger than she had expected. Just as she
prepared to release Brad and sternly criticize him for his "peeking"
... he moved.
Brad was caught by surprise ... to say the least! When his Aunt's
hand grasped his dick, he pushed his shoulders back against the couch,
his heels into the carpet and his hips up off the seat. This, instead
of helping the situation, made it more embarrassing. His Aunt's hand
reacted, holding him tighter! His pajamas outlined his hard-on so that
neither he nor his Aunt could make-believe it didn't exist. Not
knowing what to do, he froze. Searching his Aunt's features for a hint
of direction, his mind raced. "How could I be so stupid! Aunt Sharon
must realize I was peeking at her tits. She'll probably send me back
home and tell mom. I'll be grounded for life! Before he could
apologize, she released him, then spoke.
"Well, I think we'd better talk! I want you to tell me what you were
doing to cause that erection. We can't have you in a constant state of
arousal just because your living with me. I'm not going to dress like
a nun, just because your here. I expect you to tell me every thing,
young man and it better be the truth! What have you got to say for
yourself?"
With his head down, Brad began. He explained he had really been awake
and had observed Sharon "playing" with herself in the car. He stated
it was the first time he had seen a woman tease herself and he not only
became excited but also came to realized his Aunt was more than just
his Aunt, she was a very sensual woman. Now, he admitted, he was
sexually turned on by her. Next he told Sharon how he had stolen looks
down the top of her pajamas and while he hadn't really seen anything,
just knowing what was there, caused his dick to become semi-erect.
Then, when she had leaned back and he saw where her nipples were
pushing against the material, he had lost control. His dick became
rock hard as his mind visualized the pouting nipples hidden behind the
material of her pajama top! After admitting all, he said.
"Aunt Sharon, I'm really sorry! I didn't mean for this to happen, it
just did. I can't help thinking about women and their bodies ... and
yours especially. Your the prettiest and most sexy woman I know! I
love you! Please try to understand, I can't be the only boy or man
that has stared at you, your so absolutely beautiful men must stare at
you constantly. Even before I came to live with you, I would fall
asleep and dream you were my girlfriend. Whenever you visited I would
be in seventh heaven. I love the way you look and smell and especially
how you hug me. I know I shouldn't get sexually excited when I'm near
you because your my Aunt, but sometimes I just can't help myself. If
you let me stay, I promise to control my feelings and I won't try to
'peek' at you. I love you, even more than mom. Please give me another
chance?"
Sharon didn't know what to say or do. Her plan had been to embarrass
her nephew and maybe even punish him for his actions. After hearing
his reasons, she realized she was also at fault. If she hadn't exposed
herself in the car and "played" with herself, maybe he wouldn't have
changed his perception of her. It was obvious, he had a "crush" on
her. On top of everything else, she liked it! Sharon realized her
nephew was in the throes of puberty and remembered how strong her own
emotions had been when she went through it. "He actually thinks I'm
the prettiest and sexiest woman in the world!", she mused. "I've got
to do something, I can't let this continue all summer, but what?"
Looking at Brad, she began. "Brad, what you saw in the car was wrong.
It wasn't wrong that I did it, it was wrong that I did it when you were
there! Women masturbate as much as men. We have sexual needs also.
So for what you saw me do in the car, I apologize. But you had a
responsibility, as my nephew, to not look, or to "wake-up". Tonight,
you compounded the problem by your peeking at my breasts and by
thinking of me as a sex object. Women are not "toys" for men to play
with or to use. I believe you're sorry and will try not to let this
happen again, but you must be punished. If you agree to a serious
spanking, I'll forget this incident and give you one more chance."
Brad interrupted, "Oh Aunt Sharon, if you give me another chance, I'll
take whatever punishment you think is fair!"
"Don't agree too quickly, this will be a serious spanking. I can't and
won't allow you to think of me, your Aunt, as a sex object. Also, I
want you to re member this spanking so that if you get tempted again
... you'll change your mind."
Lowering his head, he said. "Aunt Sharon will you give me the spanking
I deserve?"
"Since you asked so nicely, yes. Now, go upstairs to my bedroom, take
off your pajama bottoms and wait for me."
Brad was stunned, he hadn't expected a "bare-bottom" spanking, but from
the look on his Aunt's face, he knew better than to protest. Realizing
he had no other option, he headed for his Aunt's bedroom.
Why Sharon had decided to administer a spanking she had no idea. It
had flowed out in the discussion and at the last moment, she realized
that the embarrassment of it being on his naked butt would go a long
way to wards curbing his desires for her. She also decided to wait
about ten minutes to heighten his fear. Lighting a cigarette, she
remembered the spankings she had received as a child. The last one had
been administered by her mother at sixteen. Her mother had caught her
smoking behind the garage. She had enjoyed the spanking, even though
it was painful. Putting out the last of her cigarette, she went
upstairs. Entering her bedroom, she moved to her vanity and sat with
her back to the mirror. Not saying a word, nor looking anywhere other
than at Brad's face, she motioned him to place himself over her knees.
Brad had used his hands and the tail of his pajama top to cover himself
so his Aunt wouldn't see his crotch. Moving to her satin covered lap,
he positioned himself across it. His cock and balls falling into the
opening between her satin covered thighs. The shock of the first slap
was a surprise. His Aunt wasn't holding back, as he had hoped. With
each succeeding fall of her arm the pain increased, but he soon
realized, it was also exciting. To be spread across a sexy woman's
satin covered lap, with her in total control, made him momentarily
forget the pain. Now he felt his dick rubbing against her satin
covered thighs. Feeling his cock become hard he began to take pleasure
in each stroke, since her thighs moved in response to the swing of her
arm.
Sharon had initially intended 10 slaps, 5 on each buttock. As each
stroke fell she realized she was enjoying herself. Then when she felt
his hardness between her thighs, she understood he was enjoying it
also. She knew she should stop ... but her own sense of enjoyment
wouldn't allow it. It felt exciting to have her nephew under her total
control. She was now treating the youth as a sex object for her own
satisfaction. When her arm began to tire and she sensed his needs
rising, she stopped. Reaching behind her, she grabbed the jar of
Noxema from her vanity. Unscrewing the lid, she inserted two fingers,
scooped out a generous amount and began to rub it into the flame-red
skin of Brad's butt-cheeks. Explaining to him that this would help
"cool-down" the pain. It would also give him enough time for his cock
to shrink, thereby eliminating her having to recognize the punishment
hadn't worked. Sharon had decided Brad would receive more spankings in
the future and didn't want him to realize she had noticed his
enjoyment. When she no longer felt the hardness between her thighs,
she released him. He stood before her, both hands massaging the cheeks
of his ass, no longer concerned about his nudity. Sharon, risking a
look at his equipment was impressed that one so young was so well
endowed. When she asked him if he had learned his lesson, she received
his promise and then sent him off to his room, but not before she took
a final look at his cock. After he left, she shut the light and
brought back the memory of Brad's spanking. With a smile on her lips,
she fell soundly asleep.
Brad, left her room, not even bothering to put on his pajama bottoms.
The first thing he did upon entering his room was to stand before the
full-length mirror and examine his rosy red ass. Touching the tender
skin, he said aloud.
"Boy, when she gives a spanking, she's serious about it!" Then thinking
back on what had occurred, he smiled and said. "It's a good thing Aunt
Sharon never saw my hard-on, I can imagine what that would have cost
me."
Deciding to try to sleep away the burning pain, he stretched out across
the bed. Not bothering to cover himself, he lay there going over the
exciting events of the day. The last thing he remembered, as he fell
asleep, was his hard-on rubbing between his Aunt's satin covered
thighs.
Part IV
The next morning, they both slept late. Sharon made them a quick
brunch and all was well again between the two, the events of the
previous night forgotten. Sharon, during the meal, explained his new
duties around the house and asked how his butt felt. After being
assured that the pain was mostly gone, she stated she had a few errands
to run before her dentist appointment. When she returned, she planned
on taking him shopping. She explained.
"I'm sure you didn't pack enough clothes in those two suitcases, so
let's get a late lunch and go to the mall and get you some additional
clothes to last through the summer."
Brad asked if he was to go with her on her errands? Aunt Sharon said
she usually had to sit and wait at the dentist's office, so if he
didn't mind being alone, she would come back and get him after she
finished at the dentist's. This suited him much better.
When she left, he went to his room and began collecting his feminine
attire. Then a thought came to him, "Why don't I take advantage of
Aunt Sharon's absence and do a bit of snooping. She said she wouldn't
be back for about three hours. If I don't find anything interesting
I'll still have time to change into Lynn (his alter ego)."
As he walked towards his Aunt's bedroom he passed the spare bedroom
where Sandy kept her stuff. Trying the door, he found it unlocked. He
decided to investigate that room first. If he disturbed something in
the friend's room, he rationalized, it was less likely to be noticed
and/or questioned. Opening the door, he discovered the room was almost
a duplicate of Aunt Sharon's, as feminine, just done in different
colors. Opening the door of the walk-in closet, he found the light
switch and flipped it on. It was not what he expected! The closet was
half-filled with dresses, skirts, blouses, etc. He had expected only a
few outfits, just enough for his Aunt's friend to get by on when she
visited. The woman could have lived here for a month or more with all
these clothes. Looking at some "built-in" shelves, he was again
pleasantly surprised. They held four or five different wigs, all in
different styles and shades and a collection of sweaters. The sweaters
were packed in clear plastic zipper bags. In addition, there must have
been twenty pairs of shoes, mostly high heels.
"This is going to be wonderful! I can dress-up and Auntie will never
realize it!"
Stripping to his shorts, he select a dress and held it up against his
body. It looked to be almost a perfect fit. Maybe a bit long, but
heels and my false breasts will raise the hem, he mused. Replacing the
dress, he selected one outfit after the other. Picturing himself in
each, he began to get excited over his new-found treasures. Where
before he had had a few outfits to change into, now he realized Lynn
had, for all in tents her own complete wardrobe. Each succeeding
outfit raised his level of excitement. The different colors, designs,
materials and the variety were overwhelming.
"I wonder what lingerie Aunt Sharon's friend left here?" He said aloud.
Deciding to "see" what was available in the dresser, he carried the
dress with him and returned to the bedroom. There he lovingly placed
it upon the bed and moved to the dresser. Standing before it, he slid
open the top drawer. It was full of multi-colored bras and panties.
He immediately realized that the owner must not be concerned with
neatness. The contents had obviously just been tossed haphazardly into
the drawer and "pawed" through when she needed something to wear. No
matter how he left the "pretties", he would raise no suspicions.
"What A delightful situation!", he said aloud in his best Lynn voice.
Sliding open the next drawer, he found it contained slips and
nightgowns. This lingerie was of course much neater, but still not
necessarily sorted. Emptying the contents onto the top of the dresser,
one at a time, enabled him to study the items. The night gowns were
made of the sheerest and most diaphanous material he had ever seen.
"When this woman wears these she doesn't hide much", he thought aloud.
Unfolding a couple of items, he discovered the method the woman used to
fold both nightgowns and slips to be the same and simple to duplicate.
He knew he would have no trouble replacing everything just as he found
it. The third drawer was filled to the brim with nylons and pantyhose
in different shades and colors. These were again just stuffed in as
were the contents of the first drawer. The bottom drawer held a panty
girdle and various garter belts.
Moving to the three drawer vanity he found make-up, false eye-lashes,
brushes to apply cosmetics and in the second drawer, under some socks
... a vibrator. The bottom drawer held two book-like objects, both
covered in hand-tooled dark leather. The first was a locked diary. It
would take some careful work to get past the lock, but Brad knew he
would find a way. Maybe he could find the key to it hidden somewhere.
The idea of reading a unknown woman's inner thoughts, too strong to
resist. Opening the second book he found it was a photo album. It
held 20 vinyl pages, each page able to hold two pictures on each side.
It was about half full. The first page, an unknown woman (he supposed
it was his Aunt's friend), dressed in garterbelt and nylons, had her
head buried between the thighs of another woman dressed in the same
manner. The other woman's identity became clear in the next photo ...
It was his Aunt!
Brad couldn't believe his eyes. Here was his naked Aunt, the same
woman who had spanked him for staring at her while fully dressed,
involved in lesbian sexplay. After the spanking, he had assumed his
Aunt wasn't interested in sex, now he knew better.
"Boy, was I wrong about her!"
Quickly turning the pages he found the two women displayed in various
sensual positions. He found scenes he had never even imagined. He
could see the look on Sharon's face was one of wanton desire. After
rushing from one picture to the next, he came to the last one. Having
been in such a state of excitement, he hadn't really had time to study
each shot, he decided to go through it a second time. Flipping to the
front page again, he now looked at each photo in detail. Both women
were obviously pretty and had gorgeous bodies. Not being able to
"stand" anymore, he rushed to the john, grabbed some tissues and after
just a few strokes, came in his hand. Cleaning himself up, he then
returned to his discoveries. Looking at the clock on the nightstand he
decided there was plenty of time to try some of the outfits before his
Aunt returned. Going from drawer to drawer he made his lingerie
selections. Removing his shorts, he began the change from the male
Brad to his other persona, the female Lynn.
Placing a black lace garterbelt around his waist, he slipped the hook
into the loop and spun it around. Then balling the sheer, black
nylons, he alternately inserted one foot after the other into the
re-enforced toes. Grasping the balled-up material at the toe of his
right foot, he "slinked" it up his out-stretched leg and attached it to
the dangling garters at his thigh. Repeating the process on his other
leg. French-cut white silk panties with bone colored lace and a
matching under-wire bra, each cup stuffed with two additional nylons,
followed. A red polyester full slip and black and white trimmed coat
dress were next. Within a relatively short time he was fully dressed
as Lynn. Returning to the closet, he selected a pair of black and
white spectators which matched the dress he had selected. Turning
towards the shelves, Lynn decided upon a shoulder-length, honey-blonde
wig. Placing it on her head, she moved to the vanity. Brushing the
borrowed wig into it's pre-shaped shoulder flip until he was satisfied
that it lay just right. Deciding on which lipstick and eye-shadow took
but a second or two. A little blusher, to highlight his cheekbones and
a pair of clip-on earrings completed the transformation. Perfume was
too dangerous, he decided.
Peering into the mirror ... Lynn felt very satisfied. She actually
was quite lovely. Her natural small features went a long way towards
her "passing." Standing, she raised her hem and re-adjusted each nylon.
Holding up the skirt portion of the dress to her waist she smiled ...
no revealing bulge. Lynn had become quite adept at controlling her
hard-on whenever she wanted, last night being an exception. She had
thought about this ability. In the beginning, she got hard whenever
she crossdressed. Now, she no longer got overly excited by the gender
transformation. Lynn still desired crossdressing, but didn't get a
hard-on just because of it. She wondered if it was possible she
should've been born a girl ... but wasn't sure if that was the answer.
"Oh, right now it doesn't matter. All that counts is I can change my
gender whenever I please. After I grow-up and go out on my own, I may
look into the possibility of a sex change operation, but for now, this
is enough. Now I think I want to take a walk through the house."
Loving the way the feminine clothing moved as she walked, Lynn left the
bedroom and proceeded to walk the hallway. Back and forth she swished
the entire length of the hall. The clothes and heels fit perfectly!
This was going to be heaven living with his Aunt! Deciding she was
thirsty, she turned, walked to the circular stair case and lightly
grasping the railing, she made her way downstairs copying the style she
had seen in an old Lorretta Young movie. Halfway down, she heard a
noise and the front door opened. Caught, she had nowhere to hide! In
walked Aunt Sharon. She saw Lynn immediately. A look of surprise,
followed by one of confusion, recognition and finally amused anger.
"What are you doing? Your wearing Sandy's dress. What's the meaning
of this. Come down here, right now!"
Brad always knew his secret would someday be discovered, but still
tried to stammer an explanation. His Aunt would have none of it.
"I said get down here, now! I guess the punishment you received last
night didn't leave much of an impression."
Brad meekly followed his Aunt into the den, where Sharon sat down on
the couch and motioned him to stand before her.
"Now young man and I obviously use that term loosely, explain
yourself."
Brad explained all the crossdressing details of the last eighteen
months as his Aunt listened in growing astonishment. Noticing the
bemused look on Sharon's face, Brad took heart. Maybe she wasn't as
mad as she projected? He continued the story of his feminization and
brought her up to this morning. Sharon stopped him at this point in
the narrative and said.
"Let's go up to your room where you will show me the female clothes you
brought along with you. That way I'll know if your telling me the
truth."
Brad led the way up the stairs and down the hall to his room. Sharon,
walking behind him, marveled at how well he mimicked the mannerism and
walk of a young woman in heels. She had to admit to herself, "If I
didn't know she was my nephew I'd swear she was my niece! Look at the
way she gently rolls her hips as she walks and she really has great
legs and a fine ass! Lot's of young women would love to look that good
from the rear! Of course she doesn't look bad from the front, either.
She needs help with her tits, they're a bit off center and one is
slightly lower than the other. Plus her make-up needs work, but in
total, she's actually quite pretty. With my help, she could easily
pass as my niece." Then realizing what she had just said ... Sharon
began to softly giggle.
Brad unpacked his suitcase and displayed all the female clothes he had
brought with him. When he saw the satisfied smile on her face he
thought he might get away with not having to explain his crossdressing
in Sandy's clothes, but that was not the case. Sharon, realizing the
look of hope his eyes projected and what the look implied, dashed his
hopes and demanded he continue his story. Detail after detail of this
morning's snooping was admitted. At the last moment he decided to hide
his discovery of the diary and the photo album. Maybe he could use
them to bargain with. His silence about Aunt Sharon being a lesbian
had to be worth something, he reasoned. Finishing his story, he asked.
"What are you going to do about me, Auntie? Please keep my secret", he
pleaded.
"I need some time to think this through. Let me understand this, you
would rather be a girl than a boy. It's obvious your adept at acting
as a female and I don't suppose anything I do or say will change your
desire to crossdress. Even if I expose your crossdressing to your
mother it certainly won't solve anything. All it will do is make my
sister's life more miserable because she'll have to tell your father
and we both know what his reaction will be. I'm not sure that I can do
that to her or you. Maybe your right, maybe you should have been born
a female. Be that as it may, the question still remains, 'What do I do
about it and what do I tell your mother?'."
Brad, had a solution, but, wasn't quite sure if his Aunt was ready to
hear it. Deciding to take a wait and see attitude, he shrugged his
shoulders as his only response. Afterall, he still had the photo album
as leverage. Aunt Sharon continued.
"Right now, I'm going to let you stay dressed as a woman for the day.
Obviously, we're not going shopping. If I'm going to allow you this
gender switching you may not need more boy clothes and I'm not taking
you shopping for female clothes, at least not just yet. Also, I'm not
ready to be seen with you dressed as a girl. I will allow you to spend
the entire day showing me how well you can pass. If I'm satisfied your
that 'good' maybe we can both have some fun with your desire to be a
woman. It might be fun to have my niece visit me for the summer
instead of my nephew. That doesn't mean I'm going to forget your
snooping, or that you borrowed my girlfriend's clothes. But we'll
discuss that later. Now, what is it ... Lynn, let's go downstairs and
have some lunch."
Over lunch, Sharon explained that the dentist was called to the
emergency ward of the local hospital to assist the doctors. An
accident victim had been brought in whose face had hit the windshield
and who needed immediate dental attention. This caused the dentist to
cancel all his office appointments. When Sharon was informed of these
events by his nurse, she decided to return early and pick-up Brad.
Throughout the meal, Sharon carefully observed Lynn's movements, when
they went back to the den she told Brad she liked what she had seen so
far.
"I'm halfway to accepting you as Lynn. There are, of course, some
needed improvements in your appearance. We'll work on those this
afternoon, but before we get to that, we need to talk. Why don't you
sit here on the couch, next to me."
Lynn moved to join her Aunt on the couch. Placing her hands under her
skirt she gracefully sat down. Crossing her knees and placing her
hands in her lap, she turned towards her Aunt. It was obviously done
to Sharon's satisfaction, since she smiled at Lynn, then said.
"If I agree to your becoming Lynn on a full time basis, our
relationship is going to change. First of all, you'll have to become
my niece to everyone with whom we come in contact. You won't be able
to switch back and forth between genders. That would be confusing to
both of us and too dangerous! Since I haven't told anyone about your
visit, I'll just change the story a bit. Therefore my niece instead of
my nephew will be staying the summer. However, I'm going to expect a
higher level of obedience from you. Some of the things I might have
excused from my nephew, I won't from my niece. Brad, this is your big
chance to take on the lifestyle of a young woman over an extended
period of time. It's definitely your only chance to do so with the
help I can offer you. I am going way out on a limb for you and I
expect absolute compliance with my wishes. Any variance will be dealt
with in a serious manner. That's not to say you'll be harmed, but you
will be punished, like last night."
Brad quickly responded, with a mischievous sparkle in his eye.
"Auntie, help me to REALLY transform myself into a woman, make me your
niece and I promise the only time I'll need a spanking is when I want
to be placed over your knees."
"Aha! So you enjoyed last night, I thought so! Well, since you are
being so honest, I'll be just as honest. I enjoyed giving you that
spanking. I guess you may get more spankings than I anticipated. Are
there any other secrets you'd like to admit? If we're going to change
our lifestyle we need to be perfectly open with each other. You go
first and then I have something to tell you."
Brad surmised he knew what his Aunt was alluding to ... her secret
life as a lesbian. He now had the perfect opening in which to admit
what he knew about her sexual preferences. Because of what had already
transpired, he had decided not to blackmail Aunt Sharon. Without
further hesitation, he told her about finding the diary and the photo
album. He told her he hadn't read the diary, but had seen the
pictures. Watching the reaction on Sharon's face change from shock to
smiling embarrassment was wonderful.
As I've said, Sharon's initial reaction was one of shock. She had been
about to admit her lesbian tendencies to Brad. She had realized that
when Sandy showed up next week, their secret would have been revealed
anyway. What shocked her was Brad seeing the pictures of their
love-play together and the acts they had performed which obviously
exposed their nakedness. Explaining to her nephew she was Bi-sexual
was certainly different than letting him see her in the act of eating
another woman's "pussy". Realizing there wasn't much he hadn't seen,
she asked. "What do you think of me, are you disgusted?"
"Oh no!" He stated. "I thought the pictures were beautiful. Beautiful
and very, very sensual. It made me wish I was the lucky woman in bed
with you. I think your the sexiest woman alive. I would have given
anything to join you in those scenes. Auntie, I think I better explain
something. I'm not interested in males, even when I'm dressed as Lynn.
I'm not gay in that sense. I want to be a woman with other women."
Sharon said, "Brad, I think you better explain what you mean, I realize
you have a crush on me, but I'm confused."
"You wanted us to be honest with each other, well I can't be more
honest than I'm being now. Even before I saw those pictures I
fantasized about making love to you! Your the only woman I've dreamed
about going to bed with, sometimes as a boy being seduced by you and
other times as a young woman and your equal. I've pictured myself,
hiding under your long skirts, totally hidden from view, as you carried
on a conversation with another woman. What I would do to you would
make your legs shake and your voice crack. Other times I saw myself
sitting next to you, with your hand inside my blouse, teasing my tits,
while your other hand teased circles upon my nyloned thigh. You would
unbutton your blouse and let me suck your breasts. There, I'm sorry
I've offended you, but I finally had to tell you how I feel. I'm tired
of hiding my feelings for you!"
Sharon was momentarily taken by surprise. Her mind raced as Brad
declared his love for her. The feelings Brad had for her were
obviously stronger than she at first realized. Sharon was not one who
squandered time when a quick decision was needed. Her decision made
and without explaining her decision to Brad, she acted upon it.
"Honey, let's take this discussion upstairs and get to work on
improving your feminine appearance."
The next few hours brought about a major change in young Brad's
appearance. He was told to strip, whereupon his legs were shaved for
the first time, his pubic hair was trimmed and shaped and the hair
under his arms was also removed. Then Sharon inspected him for facial
and chest hair. To Brad's delight, no beard plucking was necessary.
He suffered through having his eyebrows formed and shaped and also his
hairline was slightly contoured into a more feminine style. Through
all this he remained nude. His hair, long for a boy, was still too
short to shape into any feminine style.
Now came the "dressing-up". Sharon had laughed uproariously when Brad
had removed his nylon stuffed bra. Telling him to take a scented bath,
she grabbed her car keys and purse and drove to the drugstore. Before
she left she warned him against playing with himself.
Within a half hour she returned carrying a large paper shopping-bag
holding her purchases. Entering the master bathroom she encountered
Brad just after he had stepped out of the tub. Seeing him, a smile
came to her lips and putting her hands together, she gave the youth an
ovation. Brad stood before her with the bath towel wrapped around his
chest and a second towel around his head in the form of a turban. The
effect was one of a flat-chested girl. Seeing his features
unencumbered by clothing and framed by the towels, she realized how
easy this transformation would be.
Dumping the contents on the bed she turned to her dresser. Searching
through the drawers she selected articles of her own for him to wear.
Handing him the selections Sharon coached him in getting dressed. When
he went to roll both nylons onto his toes, she corrected him with a
slap across his bare tush.
"That's how teenage girls in a hurry get dressed. A woman takes her
time and enjoys the sensual feel of the nylons on her toes, ankles,
calfs and thighs. She never rushes getting dressed! Let whoever is
waiting for her ... wait a bit longer. Getting dressed-up, for a
sensual woman, must always be erotic, or what's the sense of being
female. Now do it right this time."
Brad, following her direction, was amazed how much more he enjoyed the
sensations. He realized it was partially due to taking his time, but
also because his legs were now clean-shaven. Attaching the clips of
the powder blue garterbelt to the nude colored nylons, he paused long
enough to slid his hands over his hose covered legs. Telling Sharon
that she was correct brought a smile to his Aunt's lips. Inserting his
legs into the matching lacy panties, he "slinked" them up and over his
thighs and "snuggled " them into place around his ass, again taking his
time and enjoying the feel of the material as it enveloped his form.
Tucking his penis back between his thighs was the only way for the
panties to fit properly. This he accomplished with difficulty, since
he was sporting a semi-hard erection. When he finally succeeded,
Sharon came over and adjusted the fit. Handing Brad the bra that
matched the panties and garterbelt, she watched him as he clipped it in
front, twisted it around, inserted his arms and pulled it in place. As
Brad bent over to pick up the extra nylons (to fill the cups), Sharon
again slapped his now pantied ass.
"That's not how a woman bends to pick something up. She either squats,
remembering to always keep one leg slightly back of the other, knees
close together, or she bends from the waist keeping her knees locked.
You must always keep in mind, it's not the clothes that will give you
away, it's acting or moving in an improper or un-lady-like manner.
Here let me give you another example; Take a look at your nails."
Brad did as instructed and again received a slap on his pantied ass.
"See, that's what I mean, males curl their fingers into their palm to
view their nails. Woman stretch their fingers and hands away from
themselves, like this. We want to see the overview, the backs of our
hands and the polish on our nails all at the same time. See the
difference, good! Now, instead of balled up nylons, slip these into
your bra. These are your new tits. The medical term is prosthetic
breast sacks. I picked them up at the medical supply store next to
Walgreen's. They are used by women who have had breast removal
surgery. They'll give you the natural look, weight and feel of real
breasts and will move with your body as you walk."
As Brad went to insert one his Aunt began laughing.
"Not that way, it's up-side-down, here let me help you."
Brad stood still as his Aunt inserted and adjusted the gel-filled
devices. Sharon cupped her hands and lightly bounced both sides of his
form-filled bra, adjusting the straps until just the right tension and
jiggle was achieved. Satisfied, she stepped back admiring the effect.
Immediately, Brad felt the difference. There was an added weight
pulling on the bra and the straps formed the slightest indentation at
his bare shoulders. He brought his hands up under both cups and
fondled each cup in turn.
"I have tits!", he boldly announced. "Oh, this is definitely much
better than the nylons. They really feel like they're a part of me!"
As he turned he felt the momentary delay in their movement and the
correcting sway after he stopped. Taking a few steps, he felt how they
"jiggled" and bounced.
"These are wonderful! So much more lifelike. Look they even have
nipple marks you can see through my bra. Oh, thank you Auntie. This
is wonderful!"
"Your welcome, now let's work on your make-up."
The next hour was spent trying different shades of base, mascara,
lipstick and eye shadow. Sharon did all the work as Brad listened and
watched attentively. When she was finished, what she had accomplished
was a work of art! No longer was he just pretty, he was beautiful.
Sharon's skills had enhanced his original, somewhat feminine facial
features, to a new level. Looking at himself in the mirror he saw a
younger version of his Aunt. It was now obvious they were related.
Sharon, satisfied with the result of her handiwork, said.
"When you learn to do as well by yourself, nobody will be able to
discover your real gender just by your looks. I have another surprise
for you, give me your hands."
Extending his hands, Sharon began attaching the false fingernails she
had purchased. After they were set, she filed them into shape, brushed
them with several coats of red nail polish which matched his lip stick.
Leaving the room for a moment, she returned carrying a handful of
assorted costume jewelry. These were tried until the effect she
desired was accomplished. He now wore a thin gold chain hanging from
his neck, with a Kremetz Rose resting just above the rise of his
breasts. A pair of matching earrings, two cocktail rings and a thin
gold watch completed the fashion statement. Stretching his hands out
as she had been taught, she marveled at how different they now looked.
Training Brad how and where to apply perfume came next. This was
followed by teaching him the different ways to step into a dress and
also how to step into high heels. For the first time in eighteen
months Brad realized he had been putting on his heels like a boy, with
one ankle over his knee. The final step in his transformation was the
wig. Sharon went to her closet and selected a light honey-brown, long
tressed hairpiece with a flip. Placing it upon his head, she then
brushed out the snarls. The finished effect was outstanding! Walking
to a full-length mirror Brad stood there with the sweetest of smiles.
Turning to his Aunt, with misty eyes, he ran to her open arms and
expressed his gratitude. Sharon was just as pleased. When she had
agreed to the transformation, she had done so with some misgivings.
She no longer felt any doubts. Brad definitely looked better as her
niece than as her nephew. Thinking aloud, she said.
"I always wanted a daughter ... now I have one in the form of a
niece."
Part V
The rest of the afternoon was spent practicing feminine mannerisms. As
Brad became more adept, Sharon decided to discuss how their new
lifestyle would work. It was decided to pass Lynn off as an eighteen
year old. The manner in which her Aunt had transformed him, helped
Lynn to look older anyway. As the light began to fade, announcing
evening, Aunt Sharon asked.
"Would you like to go out to dinner and maybe a movie?"
Lynn's response was immediate, "I would love to go out with you! Does
that mean your comfortable being seen with me in public?"
"Yes! I have no doubt you'll pass. I know a wonderful little Italian
restaurant near the mall. They have the best pasta in town. After
dinner we can see a movie if the timing is right or we can 'window
shop' for a while. Let me freshen up a bit, first. My outfit is too
casual if your going to go dressed like that. Why don't you join me in
my room while I change? I think it's time you see what a real woman
looks like!"
Brad couldn't believe his ears. If what his Aunt was saying was true,
he was going to see her naked! Quickly following, he entered Sharon's
room. There she motioned him to take a seat on the bed. She began to
strip. When she removed her bra, Brad gasped in astonishment, bringing
another smile to the woman's lips. Wasting little time Sharon selected
new lingerie, a different dress, a pair of heels, repaired her make-up,
brushed her hair, added perfume, jewelry ... all under Brad's
attentive and never wavering view. Within forty minutes they were on
their way. Lynn had been given a black shoulder bag, a lace trimmed
hanky, tissues, a hair brush and make-up to be carried in the purse.
Her Aunt also coached her as to the proper manner to carry a purse.
When they got to the restaurant, they were informed there would be a
forty-five minute wait for a table. Deciding to wait in the lounge,
they left Sharon's name and proceeded into the bar. Others had had the
same notion and there were no seats available. Before they could
decide on a new course of action, they were offered places at a small
table by two men. Lynn was reluctant, but was forced to follow her
Aunt's lead, when she accepted their invitation. Sharon introduced
Lynn and herself and the men did the same. They gave their names as
Bob and Tony. They were in town for a convention, had been bored with
the drunken antics of their fellow conventioneers and had set out on
their own. A cabby had suggested the restaurant and here they were.
They offered to buy the ladies a drink, which was accepted. It was
obvious the guys were hoping the women would join them for the evening.
Sharon could see, that while Lynn was enjoying the flattery and
attention, she was at the same time nervous over where it might
eventually lead. Sharon decided to give her "niece" a valuable lesson
in the handling of unwanted attentions. When Bob's name was called
they asked if the ladies would join them. Sharon answered.
"Bob, I don't know for sure about you, but Tony, I KNOW your married.
We've enjoyed the drinks and your company, but let's just leave it at
that."
Disappointed, but caught, both men moved to answer the table call. As
Bob moved past Sharon's chair, he paused, smiled, then said. "I'm also
married, just didn't want you to feel so smug!"
Sharon, not to be outdone, smiled back and said. "Too bad!"
Stunned at his foolishness, Bob walked slowly away, as the two women
burned him with their laughter. Aunt Sharon went over the nuances of
how she had handled their request. She explained.
"If he hadn't tried to be a smart-ass, it would have been a gracious
way of saying, 'Thanks, but no thanks.' A woman should never be
'Bitchy' unless it's necessary, but if the moment is right ... be
'Bitchy' as hell!"
Another ten minute wait and they were shown to their table. Dinner was
excellent and the service was to the extreme. Lynn and Sharon were the
only unattached females there. Everytime either looked up, someone was
looking their way, in fact a few young men caught "hell" from their
dates after staring too often. Sharon coached Lynn to cross and
uncross her legs a number of times. She whispered.
"If you catch a man trying to look up your skirt handle it in one of
two ways. If you like the way he looks, give him a small smile, then
later, tease him by inadvertently exposing your upper thighs. If you
don't like his looks, stare him down and make him feel guilty. You'll
find it's fun to be a tease and all women are teases. Your going to
have to practice being one, even though your not interested in men. It
will help in convincing everyone your female."
Leaving the restaurant, they walked over to the cinema complex. Most
of the feature films had started and the others were of no interest.
Deciding to forget about a movie, they went window-shopping. As they
shopped, they made mental notes of different outfits that might look
good on Lynn. After an hour or so, they had enough and headed home,
planning to return the next day when the shops would be open.
On the way home, Sharon said. "Lynn, I'm very pleased by the way you
acted tonight. I was the only person who had any idea you weren't a
proper young woman. You made me proud to have a niece as feminine as
you. When we get home you'll get the reward you deserve. Tonight,
we're going to sleep together. I'm cautioning you, however, don't
expect anything. I might "cuddle" you, but that's all!"
Brad assured her he would never "force" himself upon her. She was
totally in charge, he promised. Then, with a smile, he asked.
"Aunt Sharon, I must have done 'something' wrong? Don't you think your
niece needs to be taken over your knees, with her skirt at her waist
and her panties at her ankles and spanked till her ass has a rosy red
glow to it. Maybe you should set up the camera. Wouldn't you like to
add some pictures to the album. That way we can show Sandy what we've
been doing."
"That's a delicious thought, I'm sure you'll forget to do something
correctly ... before the evening is over," his Aunt answered.
Both broke out in a fit of girlish giggles.
The End
(c) 1996 Kresha Matay